Lately, there’s been a lot of talk about leaning in. I read Sheryl Sandberg’s book and for the most part, liked it. The section about mentors really resonated with me, mostly because I realized I have one! I met Dana Cowin, editor-in-chief at Food & Wine magazine, four years ago during the New York City Wine & Food Festival. As a life-long publications nerd, I’d admired her from afar; and there I was, talking to her over brunch at the Breslin and we were hitting it off. I only see Dana a few times a year, but her genuine interest and encouragement always gives me a huge boost of confidence. She’s quite incredible– successful, creative, direct, honest and always so put together. Her support means the world to me. This spring, she suggested I do an interview series on fearless heroes. Where better to start than with my own fearless hero, Dana.

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What’s the most difficult thing you’ve had to overcome & how did you do it?

Probably quitting a really good job and admitting it wasn’t going anywhere at all. It was really hard because what came after that was the complete unknown.

I was at Vogue magazine and working for this woman I really admired. I was doing somewhat interesting stuff, but in order to have grown in that, I would have had to have been a line editor and I was never going to be a line editor. Accepting that I wasn’t good at something and I wasn’t going to be able to progress and quitting was hard. How was I going to support myself and was I ever going to be good at anything?

My college roommate indelibly told me, “You are amazing at packing a suitcase! You’re so organized and everything fits and you’re so good at making choices… you are going to have a great career ahead!” And I thought, “I’m going to have a great career because I know how to pack a suitcase?”

I did quit and I told everyone that I was going to write fiction, which I really wanted to do. And then I discovered I wan’t really good at that, either! I wrote fiction all through college… and I used to review first novels for Vogue. I really enjoyed it. I really wanted to write. But I would take a short story and every morning I would rewrite the first paragraph. I mean, by the end of six months, I had four paragraphs that were perfect, but I didn’t have a story. So, I had a double dose of failure.

The failure wasn’t the hard part, the hard part was making a change. Failing itself isn’t actually so hard because you figure that out and move on. The irony is I was right to quit that job at Vogue and I thought it was going to be the end of my career in magazines. And it wasn’t, because that same editor that I adored moved to House and Garden and she rehired me. At the time, it was my absolute dream job. She put me in a position where I wasn’t responsible for line editing copy. What seemed like was the end of everything as I knew it was only a pause.

It’s the August 2014 Food & Wine magazine… you should probably pick up a copy.

I completely get that—because you find yourself defined by what you do. Especially when you land such a cool job out of college.

I wasn’t so concerned. Vogue is an extraordinary magazine. I was working with incredibly talented people. So many of those people are running their own magazines today… somehow I wasn’t as concerned about the status I would lose, which I did. When you suddenly don’t have that job, you don’t go to the same parties and people aren’t as interested in what you are doing.

I was really worried that I would never, ever, ever figure out what to do with my life. That was why it was so hard to make that move, because I could have kept going without quitting and life would have unfolded in quite a different way. It would have been potentially safer, but it turned out I just couldn’t do it anymore. It was scary, but better.

What would you say to someone who knows they need to make a change, but is having a hard time finding the courage to do it?

I had plan A, B, and C, and I think if you want to make a really big change, that somewhere in the back of your mind you need to have plans. I did quit and I did want to write fiction and I did write fiction. At the same time, I lined up a relatively cheap rent and I basically found enough work to cover it.

I also gave myself something of a time limit. To quit a job to write fiction? Really? Putting some sort of timeframe on it is good because it’s a little bit less scary. You quit because you hate something and you follow your dream… but at some point, your dream hits that midnight moment and it’s over and you do something more practical. After six months in limbo, I started applying for jobs. I got a transitional job, but just believing there is something better than what you are doing is a great motivator. Don’t do it without planning how you’re going to pay your rent and eat. I do think that jumping blind is not a great idea and I don’t think that a lot of people probably do that… but it’s also easier than you think. Figure out how cheaply you can live and how much happier you would be living less well, depending on what well means to you, and create an opportunity for yourself to find what you want. I know a lot of people rush from one job to another because they think it’s really important to be employed. It can be very depressing to be unemployed, but I think it’s more depressing to be badly employed.

Dana and I at the launch party for this book I wrote one time.

Who is your fearless hero?

My grandmother. She was born in Duluth, Minnesota. She was very brave. She came east to college and then she went on to law school. My grandmother was born in 1901 and went to law school in the 20s. Nothing would stop her. Any time you ever tried to make an excuse to my grandmother, she would just scoff. The notion that there is no reason ever in your life to make excuses, you can make anything happen, I think comes partly from her. She was incredibly direct. Incredibly honest. A lot of people have fluff around them. She was not unkind at all, but she was so direct. I’m not sure that I am as direct as she, but as a model for saying what you think and just not being caught up in anything except what really matters, she is a such a role model. She went on to work as a pro-bono lawyer for children in need in the Bronx. I have a similar desire to help other people if I can, and I think that is from her. To be a woman working in the Bronx, to be a lawyer, I think that she was pretty fearless to be doing that too. In fact, I named my daughter after her [Sylvie].

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Huge thanks to Dana for being my very first Fearless Hero feature. Who is your fearless hero & why? Comment here or email me at heyeleanorproject [at] gmail.com.